Rumors of the wristwatch’s death have been greatly exaggerated. Sure, a watch is an anachronism in this age of ubiquitous cell phones and computers that display the time. Yet, the centuries-old art of horology continues to capture the imagination, fascination and, yes, the money of men around the world.

If you set out to build a collection of wristwatches, there are several types that should be included — the dress watch, the chronograph, the dive watch, the complication watch, the beater watch, the vintage watch, and the modern haute horology watch. This series will cover each of these genres in detail and offer up our picks for the ultimate example of each. We don’t expect everyone to agree with us, so feel free to tell us your choices. Just don’t expect us to agree with you.

You have your dress watch, your diver, your chrono, your modern, and your complicated watches. Now it’s time to put the cherry on top of your watch collection and grab a piece of history, an icon and an investment. It’s time to add a vintage watch. The right vintage watch is your entry pass into a small world of connoisseurs, and marks you as a mature collector. But be careful: Acquiring a vintage watch can be a slippery slope and, before long, you may find yourself with a safety deposit box full of select rare pieces.

The quest for the right vintage watch is as much about the journey as it is the destination. Everyone has his own Holy Grail vintage piece and his own reasons for wanting it. For some, it is a watch built in the year he was born — a so-called “birth year” watch. For others, it might be a watch commemorating a certain hero or event, like an Omega Speedmaster “moon watch” from 1969. Whatever the motivation and whatever the watch, tracking down, researching and buying that special piece is not as easy as the drive to the dealer. But when it arrives, it will feel better than any of the new watches you have bought.

Because the hunt for a vintage watch can be so personal, it is difficult to name the ultimate piece to add to a collection. There are several watches that are coveted by collectors more than others. “Pre-moon” Speedmasters — i.e., those examples built prior to the 1969 Apollo 11 mission, which used a different movement than those that came after, are particularly loved. Then there is the “James Bond” Rolex Submariner, the early version of the Sub that was worn by Sean Connery in the early James Bond films. Numerous Patek Philippes occupy the rarefied space of vintage pieces that command top dollar at auctions. And among military watch aficionados, any number of watches issued to fighting forces, complete with caseback stock numbers and issue markings are bought and sold for princely sums. But pressed to select one to include in our ultimate watch collection, we have chosen the Rolex Cosmograph Daytona, reference 6239, aka the “Paul Newman” Daytona.

Caveat emptor

Buying a vintage watch is a sort of rite of passage for a collector. While you can walk into a watch dealer and plunk down your Centurion card and walk out with any of the contemporary pieces we’ve featured in this series, to acquire a vintage watch takes research, patience, some know-how, and the right timing. The rise in popularity of vintage watches and the stratospheric rise in value of them have spawned countless fakes. If you don’t do your due diligence, you could easily find yourself with a Frankenwatch, a piece cobbled together from disparate components of questionable authenticity.

How do you spot a fake when shopping for a vintage watch? That's next...